On Quitting a “Dream” Job and Entering My Attitude Era
The Circumstances That Taught Me I’m Good Enough
Early this year, I started working with poet Iain S. Thomas. (Not the “dream” job we’ll be discussing.) My job was simple: populate his social media with as much of his poetry as I could. I quickly found that my favorite of his work wasn’t one of the best-sellers. My favorite book of his became, “How to Be Happy: Not a Self-Help Book.” It earns this honor in a single quote:
“Did I ever tell you how hard my father worked so we’d be ok? That’s what I think of artistic integrity.”
That quote is in the process of changing my life. But it wouldn’t start until a few months after I read it. It was a change I couldn’t really articulate before last night when I was working on a paper for a writing class.
The paper was supposed to be on an impediment to writing. I chose “money” as my impediment because I’ve never been able to reconcile art and business emotionally. I know, factually, that it’s okay for art to make money. Unfortunately, I’ve grown up in a world where artists aren’t supposed to say that. That’s supposed to be the quiet part.
That quote from Iain started to change how I view this. It took a long journey in just a handful of quarantined months to set in. This is the story of how I learned to trust myself, trust that I’m good enough, and be okay with failing.
It sucked.
The Freelance Dance
Like every freelancer, I often long for financial stability. There’s something incredibly nice about knowing where your next paycheck is coming from. When it will come. How much it will be. At the beginning of the year, my finances were rickety at times. I was stringing together one-off gigs, and nearing the bottom of the barrel. I was a few missteps away from financial ruin. I’m still somewhat in recovery.
While I found my feet early in the year, by the time Spring rolled around I was starting to plan ahead a bit more. I knew I didn’t want to keep doing the freelance dance all the time. I needed a break from it. There was two ways to do this: get a job, or create scalable income.
I decided to do the former before the latter. I didn’t trust that I could create scalable income streams before it was “too late.”
While on the job hunt, I started writing a novel. The idea for it had come to me on a whim, and I wasn’t writing as much. A free keyboard meant I had the burning desire to do something “just for fun.” I knew in the back of my mind it could become a scalable income stream, but that was far off. I finished the rough draft of the novel in late June.
Also in mid-late June, I secured what I thought was a dream job. For obvious reasons, I won’t be naming names. The company was just getting off the ground, a small team, working on an important problem. I was excited to join and thought the founding team was great. We were in limbo on an official title, but it was going to be something cool like, “Marketing Director” or “Head of Marketing.”
It was going to be great.
Developing an Attitude Problem
Not long into starting the job, I came back to Earth a little bit.
I started to burn out quicker than a booster off a rocket ship. There was a litany of reasons for this, internal and external both to me and the job. First and perhaps most importantly, there was the whole “pandemic” thing going on. New York was very much in lockdown, and that meant my mood could swing pretty heavily. Something about being stuck inside isn’t conducive to a healthy work environment.
Around that same time, my grandfather (whom I lived with) started a fairly rapid health decline. To be honest, I’m still not entirely sure what was happening. It seemed like he was growing weaker day to day. He would eventually be hospitalized and gain candidacy for an experimental heart surgery. He wouldn’t receive the surgery and passed away only a few weeks ago.
At work, things weren’t going swimmingly. Deadlines for releases seemed to be changing all of the time. The founding team was having some arguments between them, leading to back and forth burn out. Miscommunication around the completion of projects was getting in the way of things. Everything I was doing was under a magnifying glass, with reports often not getting back to me until well after the fact.
Additionally, my personality wasn’t a good fit for the whole team. I think it was for the founder, but not for some other important members of the team. I have a tendency to be energetic, headstrong, and focused on forwarding progress at all times. This is what makes me who I am in my career, but doesn’t always mesh well. I am a fan of open and honest communication even when that communication becomes argumentative. I want to look for the solution of a problem together and believe debate leads to that.
With the magnifying glass on and the communication stymied, I felt like I was trapped. And that was one of the problems I was trying to solve in getting the job. My feelings then and now are that I have the skill set to run the ship, and I wanted that opportunity.
The Attitude Era and a Therapy Journal
What I maybe wasn’t aware of was just how bad I wanted it. It became one of the most important things in my life. Which is probably incredibly toxic. Luckily, I caught it before it got out of hand.
When quarantine started, my therapist (through BetterHelp, she’s amazing) suggested I start using the journal. I did, and found it very productive. For me, being able to document and re-read my feelings was a revelation. In the BetterHelp app, you’re asked to tag each journal entry with an emoji. I went, one day, to start a journal and noticed something:
When I was doing the freelance dance and failing at it, I was self-reporting neutral to positive emotions.
When I was at this job, I was self-reporting negative emotions almost daily.
Beyond that, my grandfather was getting worse. I knew I needed to make a change. I decided to pick up something in mid-August that I hadn’t since June: the book.
When I started reading it again, I felt like it was the best thing I’d ever read. Certainly, the best I’d ever written. I thought I wasn’t supposed to feel that way. Then I started to think about my attitude on everything. That word, for me, is always associated with wrestling.
In the late 90s, the WWE (then F) went through “The Attitude Era.” If you’ve watched any wrestling, it was probably from around that time. This was the era of The Rock and “Stone Cold” Steve Austin, which dominated TV ratings for a handful of years. It can be earmarked by plenty of things — a plethora of regrettable, edgy, lust-fueled storylines are in the mix. But The Attitude Era is also known for being one of the most enterprising, meritocratic periods in wrestling.
With competition at the top, everyone in wrestling had opportunity in front of them. Take advantage of one opportunity, and you were going to get more — both WWF and WCW needed it. (ECW, too, of course.) And with opportunity came money and honors. The “Attitude” might have referred to the mature content on the surface, but it was also about the tone laid over everything.
The Attitude Era is about working with confidence and a bit of reckless abandon to create and maximize opportunity. It was about knowing you could be the main event, and working to prove it.
So, I had to make a change.
An Attitude Adjustment
Change started as it had to: quitting my “dream” job. It wasn’t offering the opportunity I needed, and I was under no threat of creating it. And I had to go take care of my grandfather as much as I could.
That was freeing.
Then, I had to give up on worrying about my finances so much. Obviously, it’s important that ends meet, but I stopped trying to do more than that. I’m actively rewiring myself to not worry about money if my next set of bills is paid. Similarly, I’m trying not to see money as a reflection of societal value.
I am not the money I make.
Finally, I had to accept that it’s okay to be a little egotistic about my art and my work. I won’t say I’m the best writer, that’s a little above me. But I will confidently say that I could be a lot of people’s favorite writer. Therefore, it’s okay to be my own favorite writer. And it’s okay to want to sell what I’m doing.
The money can’t measure me, but it can be a way to “prove it.” If I’m good at what I do, I can earn a living doing it. Because my father worked his ass off to make sure that we’d be okay. If I fail, I’ll go work my ass off at something else. I’ve worked my ass off at this.
That was freeing.
What tied that paper I wrote together was a study that found me via a Game Maker’s ToolKit video. The study showed that students who were rewarded immediately for drawing were the most likely to stop doing it in a week’s time. Students who were never rewarded were a little bit less likely. Students who received a delayed reward were the least likely. The point: intrinsic value is more important than extrinsic value, but extrinsic value is validating.
That, to me, was permission to have a bit of an attitude. To say, “I’m going to do this because I like it. And if I make it make money later, that’s only proof I’m right.” It’s okay to work your ass off because you enjoy the work, or because you have something to prove.
And if you keep working, you might sell a few books and feel a little bit right.
And that’s freeing.
